This may not necessarily be a Calibre question, but it seems like a good chance that Calibre people will know the answers...

I can't be more pleased with Calibre from an "at home" perspective. It has solved my greatest needs:

1) Overall ebook management, conversion, transfer, save, etc.
2) RSS/Feeds. Calibre is THE Killer app in this regard!
3) Even capture of Web Pages has been solved with the Instapaper recipe.

I'm having less luck in trying to map Calibre (or any other App that I'm aware of) to my "at work" needs. The biggest problem is that my work information revolves less around the web and more around email, email attachments, MS Office, etc.

The best example I can give: I might want to read attachment(s) from an email at a later time on my Kindle. The attachments could be PDF, but they are more likely to be MS Word, Excel, Powerpoint, or the Outlook email message itself.

It's not a technical impossibility to do this now. I could just convert everything to PDF, find the files on my drives, hook up my USB cable, and move the PDFs over manually. This just seems like lots of keyclicks (and an opportunity for automation as well).

The holy grail for me would be to have a button in Word, Outlook, etc. that would "transfer to kindle". This might involve sending it via email, or the file might get sent via USB if my Kindle is already plugged in.

I definitely haven't seen any utilities out there that meet my needs in this area. If anyone is aware of apps that automate this process, please let me know.

In the mean time, I have started looking at partial solutions. I found a free PDF print driver (Bullzip) that automatically saves a PDF of any printable file into a pre-defined directory without any prompts. I'm able to supress the screens that would normally come up with PDF Writer, etc. I was even able to record a macro in WORD that printed to the Bullzip printer with a single keyclick.

Not sure what to do with the files after they are generated. I tried to search for a program that would automatically sync a PC directory with an eBook reader, but came up short. Is Calibre part of the solution at this point?

It would be awesome if the PDFs could accumulate on my drive until the next time that I plug my Kindle in. The USB connection would then trigger an automatic transfer to my device. Are there any sync programs available to do this?

The best I have been able to do on this is experiment with some of the existing PDF drivers. Bullzip and PDFCreator are the most promising.

I haven't found anything with "one button uploading", but I have been able to use the PDF print drivers to convert various documents into a format that Kindle understands. Bullzip is also able to do "silent" PDF conversion. I can specify a pre-defined directory as a holding area so that I don't have to answer any questions interactively when I print to the drivers.

Other than that, I agree that this is an "unmet need" and an opportunity for a solution.

My idea was to print or copy everything during the day to c:\kindle and then one click to sync out to Kindle and take it home.

I see you have a DX so this is probably going to work better for you than it does for me. If I print to pdf from an average Word doc then I get a A4 size pdf and eye strain on the Kindle 2. I have to resize my Word doc to A5 and then print to pdf.